Decided to do all women since I see almost none here.
Alison Krauss:
The Lucky One
New Favorite
Let Me Touch You For Awhile
Down To The River To Pray
Oh, Atlanta
Bonnie Raitt:
I Can't Make You Love Me
Tangled and Dark
Slow Ride
Dimming of the Day
Come To Me
Carly Simon:
Coming Around Again
Do The Walls Come Down
Give Me All Night
Two Hot Girls (on a Hot Summer Night)
You're So Vain
Judy Garland: (specifically from "Judy At Carnegie Hall"...actually the whole album)
Come Rain or Come Shine
The Man That Got Away
After You've Gone
The Trolley Song
You Made Me Love You
Nina Simone:
Sinnerman
Ne Me Quitte Pas
I Put A Spell On You